


Something New

by campkeesley



Series: Sam and Dean and You [3]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Double Penetration, F/M, Multi, Plot What Plot/Porn Without Plot, Sam and Dean sandwich, Sweaty Dean Winchester, Sweaty Sam Winchester, Threesome, Threesome - F/M/M, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2019-07-01
Updated: 2019-07-01
Packaged: 2020-05-31 14:43:46
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,289
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19428100
Author URL: https://archiveofourown.org/users/campkeesley/pseuds/campkeesley
Summary: Sam and Dean want to try new things with you in the bedroom. You're more than happy to oblige your boys.





	Something New

Sam and Dean had been teasing you for weeks. Figuratively and literally. Small comments followed by a wink, Dean’s hand lingering on your ass, Sam’s longing looks when you walked away, not to mention the teasing in the bedroom. The Winchesters were singularly focused these days. Which meant you were incredibly aroused these days.  
The boys seemed to notice and be very appreciative of your constant state of arousal. “What’s gotten into you lately?” Sam chuckled as he kissed you softly. “Maybe it’s what she wants in her,” Dean smirked. You blushed as you turned away. Sam and Dean exchanged a cryptic look, seeming to decide on something. Sam took your hand as Dean wrapped a hand around your waist. They led you to your shared bedroom.  
“Do you trust us?” Sam asked, his puppy dog eyes watching your expression carefully. You turned to Dean who wore a similar expression. You had been a threesome in more ways than one since you met the Winchesters. You fought beside them, hunted with them and enjoyed some more intimate perks of the job. Of course you trusted them. “Of course,” you said without hesitation. Sam kissed you softly as Dean pulled off your sweater. You got lost in Sam’s kisses as you stepped out of your jeans and kicked off your shoes as Dean began to undress behind you. Dean pulled you gently from Sam, kissing you as he pulled you closer to the bed. “Can we try something new?” Dean asked softly as he his warm hands caressed your ass. You had a feeling the boys were working their way to this for quite some time.  
You had always been a bit interested in anal play but had never really gotten around to it with other boyfriends. And after seeing what Sam and Dean were working with, you were very intimidated no matter how much you wanted to try it. You looked from Dean to Sam, biting your lip, hesitating. Slowly you nodded your head. Dean’s face broke into a wide grin, his eyes sparkling. Sam looked a bit relieved. “We can stop whenever you feel uncomfortable or if it doesn’t feel good,” the boys said in near unison making you laugh.  
The boys began to work on making you as comfortable as possible.You lay between them as Dean pulled you closer to his thick cock, peppering your neck with his kisses while his warm hands caressed your ass. Sam tilted your head up to meet his lips. You relaxed against them, the warmth turning gradually to heat as Sam’s long fingers teased your entrance. Dean positioned you so that his fingers began to explore your ass easier. You were aware of Dean leaving briefly and returning. You felt Dean’s hands spread your ass as his finger circled your hole. Sam watched your expression carefully before he nodded to Dean. Sam’s fingers worked overtime to keep you relaxed as Dean began to work his finger into your tight ass. “Holy!” Dean grunted as he slid his finger in and out. You bit your lip as you got used to the new sensation.  
You had to admit the feeling of both the Winchesters laser focused on your pleasure and comfort made you feel heady with power. You looked back at Dean, watching him as he fingered your ass. He kissed you fiercely as you felt his hard cock on your ass. You nodded at him and he sat up. He pulled you to your knees. Sam kept kissing you as his fingers worked your clit. You were so ready for Dean to claim your ass. You turned to see him lubing his thick cock. Dean began to ease in as Sam watched your face, looking for any indication that you wanted to quit.  
“Ready for more?” Dean asked, his voice husky. You nodded, gulping. Sam’s graceful fingers were hitting the spot, feeling so damn good, as Dean pushed further inside you. The sensation is so new, so fucking good you can’t help but cry out. Sam stills as Dean stops. You nod at Sam as you try to catch your breath. “Ready for the rest?” Dean asks. You snap your head back. “There's still more?” you ask, causing Sam and Dean to laugh. “Oh yeah,” Dean chuckles. One of the downsides of having the Winchesters as your lovers was getting their big cocks all in you, you think to yourself.  
Dean was finally all in. You breathe. He was stretching you in a way you'd never felt before. Sam kissed you softly. “Ready?” he asked gently. You nod. Sam’s fingers continue to tease you, slipping easily inside. Dean begins to thrust slowly. He groans loudly as he grips your ass. “She good?” Sam asks. “Better than in my wildest dreams!” Dean pants. Deans thrusts deepen as does Sam’s fingers sliding inside you. He rolls your swollen bud between his long fingers.  
Dean takes your ass greedily. He begins to quicken his pace and you can’t help but want him to pound into you. But an idea begins to take root inside you and you can’t shake it. “More,” you gasp. “More?” Sam asks. You nod. Sam and Dean exchange a look. “Both of you, now. Inside,” you pant lustfully.  
Dean pulls out gently as Sam stands up and pulls you to your feet. He lifts you easily, spreading your legs and wrapping them around his thick arms. He lowers you onto his long shaft, groaning as he fills you. You ride him easily, hands curled in his long hair. Dean kisses your neck as you feel his thick cock against your ass. Sam steadies you as Dean inches in slowly. Your eyes widen. This is happening. This is really happening, you think to yourself. Sam reminds you to breathe as Dean goes full hilt. The three of you still as if to savor the moment. You’re sure many have had fantasies about this but here you were with the Winchesters, filled completely by them.  
And then they began to thrust.  
They hold you between them, lips on your neck, your shoulders, your lips. You lose track of who does what as you lean back against Dean. He grips your ass as he pumps into it. Sam holds your thighs tightly as he bounces you on his slick cock. You know you will come over and over. You scream their names as they fill you, stretch you, take you. Rivulets of sweat course down Sam’s neck. You can feel Dean’s broad sweaty chest against you. He tilts your head back to kiss you as they both pump harder and faster. You feel that delicious pressure building combining with this new sensation.  
“She’s so tight Sammy!” Dean grunts. Sam grunts in agreement. Sam holds you tightly to him as he begins to come within you. You continue to ride his slick cock as Dean begins to drain his balls in you. You come hard as Dean stills. You rest against Sam as Dean slowly pulls out. Sam pulls out and carries you back to the bed. Dean kisses you sweetly, wrapping his arms around you. “Baby, you are so good to us,” he murmurs. Sam brushes the hair from your face. You are sweaty and sore but you have never been so happily spent in your life.  
Sam’s eyebrows knit with worry. “You ok?” he asks gently. You nod, still speechless. “You know, we don’t have to do that again if you didn’t like it,” Sam says still concerned. You sit up on your elbows. “Are you kidding me?” you ask, playfully slugging his arm. “We’re only doing that from now on!” you say half joking. Dean smiled wickedly. “That’s our girl!”

**Author's Note:**

> I can't be the only on who's ever thought about this with the Winchesters, right?


End file.
